“The journey begins in Pittsfield
“I prepared for my long walk at Dottie’s Coffee Lounge, an aromatic joint in downtown Pittsfield with artwork on the walls and cheddar scallion scones the size of a baby’s head. The official trailhead for The High Road is at Bousquet Mountain ski resort on the south side of town. (Hiker parking is available at the resort.) The High Road will connect directly to downtown Pittsfield in the years ahead. But in the spirit of walking holidays, I decided to walk 3 miles from Dottie’s to the Bousquet trailhead.
“After stocking up on beef jerky and seasoned nuts at the Berkshire General Store, I warmed up with a lively amble past the traffic on South Street. The storefronts and traffic lights receded and suddenly I was wandering past cottages and leafy estates, following South Mountain Road and Tamarack Road to the foot of Bousquet Mountain. Here a High Road trailhead kiosk beckoned beside the vacant ski lifts.”